Where to Ride: The Best Bike Trails And Paths in Chicago

Where to Ride: The Best Bike Trails And Paths in Chicago

Here in Chicago, we don’t have much to complain about. But if we had to think of a few things, bumper-to-bumper traffic and packed CTA trains and buses might come to mind. Fortunately, we know of a few alternative routes to avoid all three—and all you need is a bike.

So leave your car keys, CTA pass, and fear of those all-too-familiar “we are experiencing a delay” train announcements behind and grab a helmet instead. We’re here to help you navigate Chicago’s ten best scenic bike trails and paths… without any interruptions.

  • Lakefront Trail

    Chicago Lakefront Trail
    image via Ken Ratcliff | Flickr

    Running from the South Side all the way north to Roger’s Park, it’s no surprise that this 18.5-mile trail is perhaps the most well-known and popular in Chicago. As its name implies, the trail outlines the eastern tip of the city, so you have nothing but clear views of Lake Michigan on one side, and a reminder of just how beautiful the Chicago skyline truly is on the other. You’ll also pass wetlands, dunes, beaches, bird sanctuaries, museums, and harbors, so prepare to dismount that bike a few times because you’ll probably want to take a few pics (to make your Instagram followers jealous, of course).

  • The 606 Trail

    image via Jason Kositarut | Flickr

    Think the “L,” but for people who like being active (sound familiar, anyone?). Just two years old, the 606 is home to cyclists, runners, and walkers alike in the Humboldt Park, Wicker Park, Bucktown, and Logan Square neighborhoods. The 2.7 miles of elevated trail is a quick (and fit) way to get from east to west while passing several parks, neighborhood overlooks, and an observation deck. And for all you history buffs out there, look for signs describing the trail’s background story; it used to be an old railroad track built in the 1800s, right after the Great Chicago Fire.

  • The Riverwalk

    Chicago's Best Biking
    image via Steven Vance | Flickr

    Look out, Chicagoans, because our downtown Riverwalk just got a major makeover! With new bars, restaurants, fishing perches, marinas, and even a water theater, Chicago’s newly renovated 1.9-mile Riverwalk may be one of the city’s shorter bike paths, but you won’t miss out on any action here. The Riverwalk makes it easy to bike under bridges and through the heart of downtown where you’ll be up close and personal with the city’s diverse architecture and energetic crowds.

  • North Shore Channel Trail

    Where to Bike near Chicago
    image via @themidsis | Instagram

    If you’re ever looking to bike to Evanston but are bummed that the Lakefront Trail doesn’t stretch quite that far north, fear not — the North Shore Channel Trail does. Starting in Chicago’s Lincoln Square and ending in northern Evanston, you’ll get to bike your way over asphalt, limestone, and dirt. Our favorite part of the trail is that it winds along both sides of the North Shore Channel and the northern tip of the Chicago River, so you’ll witness some wild (literally) nature views that make the mixed terrain totally worth it.

  • North Branch Trail

    image via Christina S. | Yelp

    Make a day out of this one because not only is it 33.5 miles, but you’re going to want to stop and smell the roses, too—and millions of other flowers and plants. No, we’re serious. Depending on where you start, the 385-acre Chicago Botanic Garden is either at the beginning or end of your journey. The all-asphalt path makes it easy to soar past the north branch of the Chicago River and Skokie Lagoons, a giant forest preserve, and multiple suburban golf courses. Do they make bike bags that fit golf clubs yet?

  • Des Plaines River Trail

    Des Plaines River Trail and Greenway
    image via Christina S. | Yelp

    Okay, so we’ve been mentioning the Chicago River a lot, but there are actually other rivers in Cook County (shocking, we know), and you and your bike deserve a change of scenery. Luckily, the Des Plaines River has its own trail to make it easy to accomplish. The 54.8-mile trail runs northeast from Cook County, so you’ll ride across bridges, past wetlands, and next to nature preserves until you reach the Wisconsin border.

  • The Major Taylor Trail

    Trail Bike Chicago
    image via vxla | Flickr

    Explore one of the few forest preserves in Chicago without even having to get off your bike, thanks to the Major Taylor Trail. Named after the renowned African-American cyclist and civil rights activist Marshall Taylor, this seven-mile trail paves across 257-acres of the Dan Ryan Woods and through seven different neighborhoods on the South Side. You can also find shorter, unpaved trails in the more southern parts of the Dan Ryan Woods.

  • Northerly Island Trail

    Biking in Illinois
    image via @sightnsoundchicago | Instagram

    Do you ever daydream at work about escaping to an island filled with nature, great views, and outdoor-obsessed cyclists just like you? Well, if you work downtown, why not go on your lunch break? And even if you don’t work downtown, Northerly Island (okay, it’s actually a peninsula) isn’t hard to find—it’s just east of the Lakefront Path, and slightly south of the Museum Campus. The bike path is only one mile in length, but it loops around 91 acres, so you can turn your daydreams into a reality for as long as you want (or at least until your boss starts getting suspicious).

  • Green Bay Trail

    Biking in Chicago
    image via @lilacluvss | Instagram

    Bike alongside a Metra train (racing not recommended, no matter how powerful those quads feel), on this 8.9-mile trail between Wilmette and Highland Park. There’s really no guessing as to where you’re headed on the Green Bay Trail, as each trailhead conveniently coincides with marked Metra stops. And bonus points if you happen to bike the trail during the Ravinia Festival—a string of outdoor concerts that take place in Ravinia Park from June through September, every year since 1905.

  • Illinois Prairie Path

    Illinois Prairie Path
    image via Justin Meissen | Flickr

    Thanks to its name, it’s no secret that you’ll witness many of Illinois’ restored prairielands on this path (61 miles worth, to be exact). The trail extends from Chicago to the western suburbs, reaching across three different counties (Cook, DuPage, and Kane). Oh, and don’t be shocked if other cyclists aren’t the only people you encounter; horseback riders frequent it as well, making this trail worth checking out even more.